pent-4-ynoic acid

• ChemBase ID: 53056
• Molecular Formular: C5H6O2
• Molecular Mass: 98.09994
• Monoisotopic Mass: 98.03677943
• SMILES: C(=O)(CCC#C)O
• Canonical SMILES: C#CCCC(=O)O
• InChI: InChI=1S/C5H6O2/c1-2-3-4-5(6)7/h1H,3-4H2,(H,6,7)
• InChIKey: MLBYLEUJXUBIJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pent-4-ynoic acid
• IUPAC Traditional name: 4-pentynoic acid
• Synonyms: 4-Pentynoic acid; 4-Pentynoic acid; Propargylacetic acid; Pent-4-ynoic acid; 炔丙基脲; 4-戊炔酸

Database IDs

• CAS Number: 6089-09-4
• EC Number: 228-028-0
• MDL Number: MFCD00004407
• Beilstein Number: 1742047
• PubChem SID: 162057819; 24853886
• PubChem CID: 22464

CALCULATED PROPERTIES

• Acid pKa: 4.3621902
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.6074008
• LogD (pH = 7.4): -2.3576849
• Log P: 0.5591727
• Molar Refractivity: 24.9342 cm^3
• Polarizability: 9.395901 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 54-57 °C(lit.); 54-57°C; 54-58°C
• Boiling Point: 109-110°C/30mm; 110 °C/30 mmHg(lit.); 110°C/30mm; 110°C/30mm
• Flash Point: 75°C(167°F)

Safety Information

• Storage Warning: Corrosive/Light Sensitive/Air Sensitive/Store under Argon; IRRITANT; Light & Air Sensitive & Hygroscopic
• RTECS: SC4751000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45; 26-36/37/39-45-60
• TSCA Listed: false; 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 97%; 98%
• Linear Formula: CH≡CCH2CH2COOH

DETAILS

Sigma Aldrich - 232211

Packaging
1, 5 g in glass bottle
Application
Reaction with 1-bromo-1-alkynes in the presence of a Pd catalyst yields biologically active ynenol lactones.1
Used in a synthesis of a cyctotoxic macrolide by ring-closing metathesis of a bis acetylene.

Toronto Research Chemicals - P284900

4-Pentynoic Acid is a hypoglycemic agent shown to increase liver tyrosine aminotransferase and plasma corticosterone while decreasing blood sugar in rats.

REFERENCES

• Fuller, R.W. et al.: Experientia, 29, 277 (1973)